EP0045220A1 - Procédé et composition d'essai pour la détermination du peroxyde d'hydrogène - Google Patents

Procédé et composition d'essai pour la détermination du peroxyde d'hydrogène Download PDF

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Publication number
EP0045220A1
EP0045220A1 EP81303495A EP81303495A EP0045220A1 EP 0045220 A1 EP0045220 A1 EP 0045220A1 EP 81303495 A EP81303495 A EP 81303495A EP 81303495 A EP81303495 A EP 81303495A EP 0045220 A1 EP0045220 A1 EP 0045220A1
Authority
EP
European Patent Office
Prior art keywords
oxidase
hydrogen peroxide
reaction
hydrogen
alkyl
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Granted
Application number
EP81303495A
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German (de)
English (en)
Other versions
EP0045220B1 (fr
Inventor
Akira Miike
Yoshiaki Shimizu
Toshio Tatano
Katsuyuki Watanabe
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JP Morgan Delaware
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Kyowa Hakko Kogyo Co Ltd
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Publication of EP0045220A1 publication Critical patent/EP0045220A1/fr
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Publication of EP0045220B1 publication Critical patent/EP0045220B1/fr
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    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12Q—MEASURING OR TESTING PROCESSES INVOLVING ENZYMES, NUCLEIC ACIDS OR MICROORGANISMS; COMPOSITIONS OR TEST PAPERS THEREFOR; PROCESSES OF PREPARING SUCH COMPOSITIONS; CONDITION-RESPONSIVE CONTROL IN MICROBIOLOGICAL OR ENZYMOLOGICAL PROCESSES
    • C12Q1/00—Measuring or testing processes involving enzymes, nucleic acids or microorganisms; Compositions therefor; Processes of preparing such compositions
    • C12Q1/26—Measuring or testing processes involving enzymes, nucleic acids or microorganisms; Compositions therefor; Processes of preparing such compositions involving oxidoreductase
    • C12Q1/28—Measuring or testing processes involving enzymes, nucleic acids or microorganisms; Compositions therefor; Processes of preparing such compositions involving oxidoreductase involving peroxidase
    • G—PHYSICS
    • G01—MEASURING; TESTING
    • G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
    • G01N33/00—Investigating or analysing materials by specific methods not covered by groups G01N1/00 - G01N31/00
    • G01N33/48—Biological material, e.g. blood, urine; Haemocytometers
    • G01N33/50—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing
    • G01N33/52—Use of compounds or compositions for colorimetric, spectrophotometric or fluorometric investigation, e.g. use of reagent paper and including single- and multilayer analytical elements
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12Q—MEASURING OR TESTING PROCESSES INVOLVING ENZYMES, NUCLEIC ACIDS OR MICROORGANISMS; COMPOSITIONS OR TEST PAPERS THEREFOR; PROCESSES OF PREPARING SUCH COMPOSITIONS; CONDITION-RESPONSIVE CONTROL IN MICROBIOLOGICAL OR ENZYMOLOGICAL PROCESSES
    • C12Q2326/00—Chromogens for determinations of oxidoreductase enzymes
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S435/00—Chemistry: molecular biology and microbiology
    • Y10S435/805—Test papers
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S435/00—Chemistry: molecular biology and microbiology
    • Y10S435/81—Packaged device or kit

Definitions

  • the present invention provides a method and a test composition for the determination of bydrogen peroxide using a novel chromogen as a hydrogen donor. More particularly, it provides a method for the determination of hydrogen peroxide by reacting hydrogen peroxide with the chromogen in the presence of peroxidase and determining the pigment formed,and test compositions suitable for the determination.
  • the determination of a substrate was generally carried out by oxidizing the substrate by the action of oxidase and determining the formed hydrogen peroxide.
  • uric acid is oxidized by urioase
  • choresterol is oxidized by choresterol oxidase to form hydrogen peroxide.
  • the hydrogen peroxide is determined by reacting the hydrogen peroxide with a chromogen in the presence of peroxidase to form a pigment and measuring the absorbancy of the reaction solution coloured by the formation of the pigment in the visible ray region.
  • substituted amino means mono- or disubstituted amino and the substituents are alkyl, alkenyl, aryl, hydroxyalkyl or acylalkyl.
  • the raw materials are known pigments.
  • the raw material is subjected to reduction in the presence of reducing agents such as NaBH 4 , Fe-HCl, etc.
  • the reduction is carried out in a solvent such as water, methanol, acetone, etc. at from room temperature to the boiling point of the solvent used.
  • the reduction product is isolated from the reaction mixture.
  • an acylating agent an alkylthiocarbonylating agent, ester of isocyanic acid, or ester of isothiocyanic acid.
  • the reaction is usually at from room temperature to the boiling point of the solvent used.
  • the isolation of the desired product from the reaction mixture is carried out by a suitable organic synthesis isolation means such as extraction, concentration, chromatography, recrystallization, filtration, etc.
  • a test solution containing 0.1 mg/mJ compounds indicated in Table 1, 10 IU/ml POD and if necessary, 0.1% surfactant in a phosphate buffer solution (pH 6.0) is prepared.
  • a test solution containing 20 ⁇ l hydrogen peroxide solution and the absorbancy of the coloured reaction solution (E) is measured at maximum absorption wave-length ( ⁇ max) of the pigment formed.
  • the blank absorbancy (E B ) is measured by repeating the same procedures as described above except that water instead of hydrogen peroxide solution is used.
  • the stability of colour is determined as follows. The value of (E-E B ) immediately after the reaction is discontinued (in about 30 minutes) is measured. Then the reaction solution is further incubated at 37°C for 4 hours and then (E-E B ) is calculated.
  • the .symbol “ ⁇ ” means that the decrease of the value of E-E B is 0-5% during the further incubation and "+” means that the decrease is 5-10%.
  • the maximum absorption wavelength in the visible ray region of the pigment is larger than that of hemoglobin contained in serum, which is around 400 nm and therefore, the absorbancy by the present method is not affected by hemoglobin.
  • the compound (I) or (II) and POD may be added to the system where hydrogen peroxide is produced (hereinafter referred to as "H 2 O 2 -producing system").
  • the absorbancy of the reaction solution coloured by the formation of pigment is measured in the visible ray region, 400-760 nm.
  • the standard curve showing the relation between the amount of hydrogen peroxide and absorbancy is prepared by using a standard hydrogen peroxide solution as the sample. The amount of hydrogen peroxide in the sample is calculated by applying the absorbancy obtained to the standard curve.
  • the reaction is usually carried out at a temperature of 5-50°C, preferably 25-40°C, in a buffer solution having a pH of 2-10 and completed in several minutes.
  • phosphate buffer tris-HCl buffer, succinate buffer, citrate buffer, acetate buffer, etc. may be used in a concentration of 0.005-2 mol/l.
  • the present method may be used for the determination of reactants in a, system where hydrogen peroxide is produced.
  • a, system where hydrogen peroxide is produced Particularly, when the system is an enzymatic reaction, both the H 2 O 2 producing system and the system where pigment is produced [hereinafter referred to as pigment-producing system] proceed at the same time and therefore, such a method is simple and convenient.
  • Such an enzymatic reaction includes the combination of oxidase and a substrate thereof and examples of the combination are uric acid-uricase, cholesterol-cholesterol oxidase, cholesterol ester- cholesterol esterase and cholesterol oxidase, xanthin, hypoxanthin or guanine-xanthin oxidase, phospholipase D-lecitin-choline oxidase, choline-choline oxidase, pyruvic acid-pyruvate oxidase-phosphoric acid, triglyceride-lipoprotein lipase-ATP-glycerinkinase-glycerin-3-phosphate oxidase, fatty acid-coenzyme A-acyl Co A synthetase-acyl Co A oxidase, triglyceride-lipase-glycerol oxidase, glucose-glucose oxidase and galactose-galactose
  • the substrates of these enzymatic reactions are contained in serum, urea, etc. and the determination of the substrates is useful for diagnostic purposes.
  • Another aspect of the present invention is to provide a test composition for the determination of hydrogen peroxide which comprises oxidase for the substrate to be determined, the chromogen represented by the formula (I) or (II) and peroxidase.
  • the composition may contain buffer reagent.
  • composition may contain surfactants such as polyoxyethylenealkylether, antiseptics such as sodium azide, ascorbate oxidase for decomposing ascorbic acid, etc. if necessary.
  • surfactants such as polyoxyethylenealkylether, antiseptics such as sodium azide, ascorbate oxidase for decomposing ascorbic acid, etc. if necessary.
  • 0.1M phosphate buffer solution pH 6.0
  • 10 IU/ml peroxidase 10 IU/ml peroxidase
  • 0.1 IU/ml uricase 10 IU/ml peroxidase
  • 0.1 mg/ml compound II-6 0.1% Triton X-100 is prepared as a test solution.
  • To 3 ml of the test solution is added each of 20 ⁇ l of samples indicated in Table 3 and each mixture is incubated for reaction at 37°C with stirring for 10 minutes.
  • Example 2 The same procedures as described in Example 1 are repeated except that the chromogens indicated in Table 1 are used instead of compound II-6 and the enzymatic reactions with the normal serum are carried out. . The absorbancy of each reaction solution is measured at ⁇ max for each chromogen and similar results to that with compound II-6 are obtained.
  • the reagent solution is prepared by dissolving 10 mg of Compound 11-6 in 100 ml of 0.1M phosphate buffer solution (pH 6.0) containing 15 mg of co-carboxylase, 200 IU of pyruvate oxidase, 0.1 ml of triton X-100 and 500-IU of peroxidase.
  • each containing 3 ml of the reagent solution is added (A) 0.05 ml of distilled water (B) 1 mg/dl pyruvic acid standard solution or (C) 0.05 ml of serum and each mixture is incubated at 37°C for 20 minutes. The absorbancy of each reaction solution is measured at 666 nm and the concentration of pyruvic acid in the serum is determined at 1.04 mg/dl.
  • reagent solution 100 ml of 0.05M phosphate buffer solution (pH 6.0) containing 0.1 ml of triton X-100, 100 U of peroxidase, 3.3 U of acyl Co A synthetase, 1.7 U of acyl-Co A oxidase, 33 ⁇ mol of Co enzyme A, 133 ⁇ mol of ATP, 133 ⁇ mol of magnesium chloride and 10 mg of compound II-4 is prepared.
  • the standard curve is obtained by repeating the above procedures using a standard solution of palmitic acid and distilled water as a sample.
  • the acid content in the serum is calculated at 394 ⁇ eg/l.
  • reagent solution having the same composition as that of reagent solution (1) except that 0.1 mg/ml 4-AA and 0.2 mg/ml N,N-diethylaniline is used instead of compound II-6.
  • Reagent solution (1) 3ml of Reagent solution (1) is heated at 37°C for 10 minutes and 50 ⁇ l of Reagent solution (3) is added to the solution.
  • E 1 the absorbancy of the mixture at 665 nm, which is defined as E 1 is measured.
  • E 5 the absorbancy which is measured 5 minutes after the addition
  • one g of Methylene Blue (produced by Wako Junyaku Co., Ltd.) is dissolved in 100 ml of water and one g of sodium . salt of hydrogen borohydride is added to the solution portionwise. The mixture is subjected to reaction at 20°C.
  • reaction mixture is charged on a column packed with silica gel having a size of 60-80 mesh and elution is carried out with chloroform.
  • the eluate is concentrated to dryness under reduced pressure to obtain 1.3 g of compound II-9, as a white or light brown amorphous powder.
  • the melting point of the product is 143-145°C and the infrared spectrum and NMR spectrum are shown in Figures 9 and 18, respectively.
  • Example 6 The same procedures as described in Example 6 are repeated except that the compounds indicated in Table 5 are used instead of phenylisocyanate to obtain the desired compounds shown in Table 5.
  • Bindschedler's Green Leuco Base Dotite BG, produced by Dojin Yakukagaku Kenkyusho
  • Dojin Yakukagaku Kenkyusho a Bindschedler's Green Leuco Base
  • 20 m£ of chloroform 20 m£ of chloroform.
  • Each of the compounds (isocyanates) indicated in Table 6 is added to the solution and each mixture is subjected to reaction at room temperature for 16 hours.
  • Methanol is added to each reaction mixture to decompose the unreacted isocyanate and the same purification procedures as in Example 6 are repeated to obtain the desired compounds shown in Table 6.
  • Example 5 A similar procedure to that of Example 5 is carried out except that Meldola Blue is used instead of Methylene Blue to obtain compound II-10 in an oily form.

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  • Biochemistry (AREA)
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  • Measuring Or Testing Involving Enzymes Or Micro-Organisms (AREA)
  • Investigating Or Analyzing Non-Biological Materials By The Use Of Chemical Means (AREA)
  • Investigating Or Analysing Biological Materials (AREA)
EP81303495A 1980-07-30 1981-07-30 Procédé et composition d'essai pour la détermination du peroxyde d'hydrogène Expired EP0045220B1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP103665/80 1980-07-30
JP55103665A JPS6033479B2 (ja) 1980-07-30 1980-07-30 過酸化水素の定量方法

Publications (2)

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EP0045220A1 true EP0045220A1 (fr) 1982-02-03
EP0045220B1 EP0045220B1 (fr) 1985-11-06

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US (1) US4384042A (fr)
EP (1) EP0045220B1 (fr)
JP (1) JPS6033479B2 (fr)
DE (1) DE3172825D1 (fr)

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EP0124287A3 (en) * 1983-03-31 1988-01-13 Kyowa Medex Co. Ltd. Method and test composition for determination of hydrogen peroxide
EP0162685A3 (en) * 1984-05-21 1988-01-13 Eastman Kodak Company Compositions and elements containing triarylmethane leuco dyes and methods using same
EP0210559A3 (en) * 1985-07-25 1989-02-22 Boehringer Mannheim Gmbh N-acyldihydroresorufin derivatives, process for their preparation as well as their use for the determination of hydrogen peroxide, peroxidatically active compounds, or peroxidase
US4879383A (en) * 1986-07-01 1989-11-07 Wako Pure Chemical Industries, Ltd. Urea derivatives
EP0361470A3 (en) * 1988-09-30 1990-11-22 Fujirebio Inc. Method of the chemiluminescence assay of the activity of peroxidase
EP0342984A3 (fr) * 1988-05-18 1992-03-11 Kyowa Medex Co. Ltd. Procédé pour détecter NAD(P)H
WO1996000928A1 (fr) * 1994-06-30 1996-01-11 Minnesota Mining And Manufacturing Company Composes chromogenes de liberation de colorants leuco redox pour elements photothermographiques
WO2015169511A2 (fr) 2014-05-06 2015-11-12 Diasys Diagnostic Systems Gmbh Détermination enzymatique de hba1c
CN105541756A (zh) * 2015-12-17 2016-05-04 陕西方舟制药有限公司 一种制备1-(3，7-二氨基-吩噻嗪-10-基)乙酮的方法
CN105699342A (zh) * 2014-11-28 2016-06-22 中国科学院大连化学物理研究所 一种利用滴定技术测量氧原子浓度的方法

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US20040171034A1 (en) * 2002-05-03 2004-09-02 Brian Agnew Compositions and methods for detection and isolation of phosphorylated molecules
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US8445702B2 (en) * 2003-05-05 2013-05-21 Life Technologies Corporation Zinc binding compounds and their method of use
US20050250214A1 (en) * 2004-05-05 2005-11-10 Gee Kyle R Zinc binding compounds and their method of use
EP2298312B1 (fr) 2003-10-31 2018-09-26 Molecular Probes Inc. Composés fluores de résorufine et leur application dans la détection du peroxyde d'hydrogène
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EP1987361A4 (fr) * 2006-01-30 2009-03-04 Invitrogen Corp Compositions et procédé pour détecter et quantifier des substances toxiques dans des états pathologiques
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WO2008029281A2 (fr) 2006-02-10 2008-03-13 Invitrogen Corporation Marquage et détection de protéines modifiées post-traductionnellement
JP5337691B2 (ja) 2006-04-20 2013-11-06 ベクトン・ディキンソン・アンド・カンパニー 熱安定性タンパク質ならびにその作製方法および使用方法
WO2008093722A1 (fr) 2007-01-30 2008-08-07 Arkray, Inc. Procédé de détection d'un colorant au dérivé phénothiazine et réactif pour révélateur chromogène destiné à être utilisé dans le procédé
US8586743B2 (en) * 2007-01-30 2013-11-19 Life Technologies Corporation Labeling reagents and methods of their use
US8758648B2 (en) * 2008-03-19 2014-06-24 Arkray, Inc. Stabilizer of color former and use thereof
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BR112013001400A2 (pt) 2010-08-11 2016-05-24 Kyowa Medex Co Ltd método para conservar uma solução aquosa contendo um leuco-cromogênico, método para estabilizar um leuco-cromogênio, e, reagente líquido
CA2807133A1 (fr) 2010-08-11 2012-02-16 Kyowa Medex Co., Ltd. Procede de mesure d'hemoglobine glyquee
WO2012022734A2 (fr) 2010-08-16 2012-02-23 Medimmune Limited Anticorps anti-icam-1 et procédés d'utilisation
CN103261331B (zh) 2010-12-13 2015-07-29 协和梅迪克斯株式会社 含有无色型色原体的水溶液的保存方法
EP2681196B1 (fr) 2011-03-04 2015-09-09 Life Technologies Corporation Composés et procédés de conjugaison de biomolécules
WO2015050959A1 (fr) 2013-10-01 2015-04-09 Yale University Anticorps anti-kits et leurs méthodes d'utilisation
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CA2954780A1 (fr) 2014-07-15 2016-01-21 Medimmune, Llc Neutralisation d'anticorps anti-grippe b et leurs utilisations
EP3443126B1 (fr) 2016-04-15 2023-11-15 Icahn School of Medicine at Mount Sinai Profilage de tissus par coloration consécutive immunohistochimique multiplexée
EP3492529A4 (fr) 2016-07-29 2020-12-16 Hitachi Chemical Diagnostics Systems Co., Ltd. Procédé de conservation d'une solution aqueuse contenant un chromogène de type leuco
JP6759126B2 (ja) * 2017-02-28 2020-09-23 株式会社同仁化学研究所 新規な酸化発色性化合物及び酸化発色試薬
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CHEMICAL ABSTRACTS, Vol. 89, No. 14, October 2, 1978, page 888, Abstract 122422x Columbus, Ohio, US N.V. RAO et al.: "Oxazine Dyes as New Iodometric Indicators" & J. Indian Chem. Soc. 1978, 55 (2), 200-3 * the whole Abstract * *

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EP0124287A3 (en) * 1983-03-31 1988-01-13 Kyowa Medex Co. Ltd. Method and test composition for determination of hydrogen peroxide
US4916058A (en) * 1983-03-31 1990-04-10 Kyowa Medex Co., Ltd. Method and test composition for determination of hydrogen peroxide
EP0162685A3 (en) * 1984-05-21 1988-01-13 Eastman Kodak Company Compositions and elements containing triarylmethane leuco dyes and methods using same
EP0210559A3 (en) * 1985-07-25 1989-02-22 Boehringer Mannheim Gmbh N-acyldihydroresorufin derivatives, process for their preparation as well as their use for the determination of hydrogen peroxide, peroxidatically active compounds, or peroxidase
US4879383A (en) * 1986-07-01 1989-11-07 Wako Pure Chemical Industries, Ltd. Urea derivatives
EP0342984A3 (fr) * 1988-05-18 1992-03-11 Kyowa Medex Co. Ltd. Procédé pour détecter NAD(P)H
EP0361470A3 (en) * 1988-09-30 1990-11-22 Fujirebio Inc. Method of the chemiluminescence assay of the activity of peroxidase
US5171668A (en) * 1988-09-30 1992-12-15 Fujirebio Inc. Method of the chemiluminescence assay of the activity of peroxidase
WO1996000928A1 (fr) * 1994-06-30 1996-01-11 Minnesota Mining And Manufacturing Company Composes chromogenes de liberation de colorants leuco redox pour elements photothermographiques
WO2015169511A2 (fr) 2014-05-06 2015-11-12 Diasys Diagnostic Systems Gmbh Détermination enzymatique de hba1c
US10093959B2 (en) 2014-05-06 2018-10-09 Diasys Diagnostic Systems Gmbh Enzymatic determination of HBA1c
US10202632B2 (en) 2014-05-06 2019-02-12 Diasys Diagnostic Systems Gmbh Enzymatic determination of HbA1c
CN105699342A (zh) * 2014-11-28 2016-06-22 中国科学院大连化学物理研究所 一种利用滴定技术测量氧原子浓度的方法
CN105699342B (zh) * 2014-11-28 2018-04-06 中国科学院大连化学物理研究所 一种利用滴定技术测量氧原子浓度的方法
CN105541756A (zh) * 2015-12-17 2016-05-04 陕西方舟制药有限公司 一种制备1-(3，7-二氨基-吩噻嗪-10-基)乙酮的方法
CN105541756B (zh) * 2015-12-17 2018-02-09 陕西方舟制药有限公司 一种制备1‑(3，7‑双二甲氨基‑吩噻嗪‑10‑基)乙酮的方法

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US4384042A (en) 1983-05-17
DE3172825D1 (en) 1985-12-12

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